US2110896A - Insecticide - Google Patents
Insecticide Download PDFInfo
- Publication number
- US2110896A US2110896A US2110896DA US2110896A US 2110896 A US2110896 A US 2110896A US 2110896D A US2110896D A US 2110896DA US 2110896 A US2110896 A US 2110896A
- Authority
- US
- United States
- Prior art keywords
- water
- insecticide
- cresol
- insecticides
- phenylazo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000000749 insecticidal Effects 0.000 title description 12
- 239000002917 insecticide Substances 0.000 title description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- -1 azo compound Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- MWIAHGPVFGASED-QINSGFPZSA-N (4Z)-2-methyl-4-(phenylhydrazinylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C(C)=C\C1=N/NC1=CC=CC=C1 MWIAHGPVFGASED-QINSGFPZSA-N 0.000 description 4
- 241000256113 Culicidae Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 210000004940 Nucleus Anatomy 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 244000144730 Amygdalus persica Species 0.000 description 2
- JCZUIEHTNMQCRK-UHFFFAOYSA-N CHEMBL1993024 Chemical compound C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 JCZUIEHTNMQCRK-UHFFFAOYSA-N 0.000 description 2
- 206010022114 Injury Diseases 0.000 description 2
- UWRBYRMOUPAKLM-UHFFFAOYSA-L Lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 240000005158 Phaseolus vulgaris Species 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000012055 fruits and vegetables Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000266 injurious Effects 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000003000 nontoxic Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002588 toxic Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
Definitions
- This invention relates to improvements in materils for destroying a checking the growth or multiplication of living organisms, whether plant,
- An object of the invention is to provide materials suitable for use as insecticides,
- Another object of the invention is to provide a material for dusting or spraying delicate vegetation such as bean plants, peach trees, and plants grown under glass, which will not cause injury to foliage. 4
- Another object of the invention is to provide a material which is relatively non-toxic to man and domestic animals when taken by mouth, and which can be used in place of lead arsenate and other arsenicals for destroying insects without leaving harmful residues on fruits and vegetables.
- aryl hydroxyazo compounds may be applied in a manner similar to that in which insecticides in general are used, that is, as dusts, or in the form of solutions or suspensions in various media, such as water, kerosene, etc., and either with or without the use of spreaders, wetting agents, or sticking agents.
- R1 and R2 denote interchangeable homocyclic aryl nuclei, R1 being a single benzene ring 1.
- An insecticide comprising a compound of e general formula:
- R2 a naphthyl nucleus
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Patented Mar. 15, 1938 UNITED STATES PATENT OFFICE msnc'rrcmn America No Drawing. Application June 27, 1936, Serial No. 87,742
3 Claims.
(Granted under the act of March 3, 1883, as amended April 30, 1928; 370 0. G. 157) This application is made under the act of March 3, 1883, as amended by the act of April 30, 1928, and the invention herein described, if patented, may be manufactured and used by or for the Government for governmental purposes without the payment to us of any royalty thereon.
We hereby dedicate the invention herein described to the free use of the Public in the territory of the United States of America to take effect upon the granting of a patent to us.
This invention relates to improvements in materils for destroying a checking the growth or multiplication of living organisms, whether plant,
or animal, which are economically injurious to man.
An object of the invention is to provide materials suitable for use as insecticides,
Another object of the invention is to provide a material for dusting or spraying delicate vegetation such as bean plants, peach trees, and plants grown under glass, which will not cause injury to foliage. 4
Another object of the invention is to provide a material which is relatively non-toxic to man and domestic animals when taken by mouth, and which can be used in place of lead arsenate and other arsenicals for destroying insects without leaving harmful residues on fruits and vegetables.
We have found that substances belonging to a certain class of organic compounds have a specific toxic effect upon harmful insects and our invention consists in the application of said substances to the destruction of insect pests.
The novel insecticides found by us belong to the class of organic compounds which contain in their molecules, according to accepted formulation, two homocyclic nuclei joined by an azo linkage, that is, by the -N=N- group, and which contain, in addition, one or more hydroxyl groups, together with one or more alkyl or aryl groups.
Typical representatives of this class ofconb pounds are:
4-Phenylazo-o-cresol:
I V H:
i-Phenylazo-m-cresol:
HaC
' cm i 1-(p-Tolylazo)-2-naphthol:
do not affect the novel features claimed.
For specific examples of the toxicity of these compounds it may be stated that when 4-Phenyl- .azo-m cresol was dissolved in acetone and the resulting solution poured into water there resulted a 90% mortality of culicine mosquito larvae within 16 hours when the concentration of the azo compound was one part to 50,000 parts of water.
When 4-Phenylazo-o-cresol was dissolved in acetone and the resulting solution poured into water there resulted a 98% mortality of culicine V mosquito larvae within 16 hours when the con-' centration of the azo compound was one part to 25,000 parts of water.
The above examples are not to be construed as limiting either the method of application of these novel insecticides or the kinds of insects to which they may be applied. 7
These aryl hydroxyazo compounds may be applied in a manner similar to that in which insecticides in general are used, that is, as dusts, or in the form of solutions or suspensions in various media, such as water, kerosene, etc., and either with or without the use of spreaders, wetting agents, or sticking agents.
Having thus described our invention we claim:
Where R1 and R2 denote interchangeable homocyclic aryl nuclei, R1 being a single benzene ring 1. An insecticide comprising a compound of e general formula:
DONALD L. WVIAN. Ii-mRBERT L. J. HALL-ER.
and R2 a naphthyl nucleus.
Publications (1)
Publication Number | Publication Date |
---|---|
US2110896A true US2110896A (en) | 1938-03-15 |
Family
ID=3429306
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US2110896D Expired - Lifetime US2110896A (en) | Insecticide |
Country Status (1)
Country | Link |
---|---|
US (1) | US2110896A (en) |
-
0
- US US2110896D patent/US2110896A/en not_active Expired - Lifetime
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